US10336783B2 - Solid catalyst for hydride isomerization reaction in an aqueous medium - Google Patents

Solid catalyst for hydride isomerization reaction in an aqueous medium Download PDF

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US10336783B2
US10336783B2 US15/124,939 US201515124939A US10336783B2 US 10336783 B2 US10336783 B2 US 10336783B2 US 201515124939 A US201515124939 A US 201515124939A US 10336783 B2 US10336783 B2 US 10336783B2
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phosphoric acid
element oxide
oxide
fructose
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US20170022238A1 (en
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Michikazu Hara
Kiyotaka Nakajima
Daiki TAKEDA
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Japan Science and Technology Agency
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
    • C07H3/02—Monosaccharides
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
    • B01J21/02—Boron or aluminium; Oxides or hydroxides thereof
    • B01J21/04—Alumina
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/08—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of gallium, indium or thallium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/14—Phosphorus; Compounds thereof
    • B01J27/16—Phosphorus; Compounds thereof containing oxygen, i.e. acids, anhydrides and their derivates with N, S, B or halogens without carriers or on carriers based on C, Si, Al or Zr; also salts of Si, Al and Zr
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/14—Phosphorus; Compounds thereof
    • B01J27/16—Phosphorus; Compounds thereof containing oxygen, i.e. acids, anhydrides and their derivates with N, S, B or halogens without carriers or on carriers based on C, Si, Al or Zr; also salts of Si, Al and Zr
    • B01J27/18—Phosphorus; Compounds thereof containing oxygen, i.e. acids, anhydrides and their derivates with N, S, B or halogens without carriers or on carriers based on C, Si, Al or Zr; also salts of Si, Al and Zr with metals other than Al or Zr
    • B01J27/1802—Salts or mixtures of anhydrides with compounds of other metals than V, Nb, Ta, Cr, Mo, W, Mn, Tc, Re, e.g. phosphates, thiophosphates
    • B01J27/1811—Salts or mixtures of anhydrides with compounds of other metals than V, Nb, Ta, Cr, Mo, W, Mn, Tc, Re, e.g. phosphates, thiophosphates with gallium, indium or thallium
    • B01J35/002—
    • B01J35/1014—
    • B01J35/1019—
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/30—Catalysts, in general, characterised by their form or physical properties characterised by their physical properties
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
    • B01J35/61—Surface area
    • B01J35/613—10-100 m2/g
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
    • B01J35/61—Surface area
    • B01J35/615—100-500 m2/g
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/28—Phosphorising
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives

Definitions

  • the present invention relates to a solid catalyst working in an aqueous medium to catalyze a hydride isomerization reaction of glucose, and a use thereof.
  • a biomass is a renewable resource, and is regarded as a promising novel carbon source to replace crude oil.
  • glucose is produced from a variety of plant materials, and it is known that 5-hydroxymethylfurfral (HMF) obtained through dehydration of glucose can be a raw material of useful chemical substances such as furfuryl alcohol and tetrahydrofuran.
  • HMF 5-hydroxymethylfurfral
  • As a reaction for producing HMF from glucose a method in which glucose is converted into fructose through a hydride transfer reaction, and the fructose is dehydrated to produce HMF is widely employed.
  • the reaction using the Sn-containing ⁇ -zeolite causes, however, a large number of side reactions, and not only fructose and HMF but also a large number of products are generated, and hence this method is not industrially applicable.
  • Sn has a safety problem, and cannot be used for producing fructose to be used in food.
  • aluminum phosphate is low not only in catalytic activity but also in fructose selectivity, and hence is difficult to apply as an industrial catalyst.
  • an object of the present invention is to provide a novel catalyst capable of selectively catalyzing, in water or in an aqueous solution, a desired hydride isomerization reaction from glucose to fructose.
  • the conversion reaction from fructose to HMF satisfactorily proceeds in a Brönsted acid, and therefore, if the conversion reaction from glucose to fructose can be selectively performed, the process can be industrially advantageous as a whole, and the fructose can be applied also to food such as a sweetener.
  • the present inventors have studied solid catalysts capable of causing conversion from glucose to fructose to selectively proceed in an aqueous medium, and have found that a catalyst obtained by treating, with phosphoric acid, a surface of a group 13 element oxide such as aluminum oxide causes a hydride isomerization reaction from glucose to fructose to selectively proceed in an aqueous medium, and thus, the present invention was accomplished.
  • the present invention provides the following [1] to [5]:
  • a solid catalyst for a hydride isomerization reaction from glucose to fructose performed in water or in an aqueous solution, comprising a group 13 element oxide whose surface has been subjected to a phosphoric acid treatment.
  • [5] A method for producing fructose, comprising allowing the catalyst according to any one of [1] to [4] to work on glucose in water or in an aqueous solution.
  • a catalyst of the present invention is useful as a solid catalyst having high selectivity for a hydride isomerization reaction from glucose to fructose performed in water or in an aqueous solution. According to a method of the present invention, fructose can be obtained with high selectivity from glucose through a reaction performed in water or in an aqueous solution.
  • FIG. 1 illustrates XRD spectra of aluminum oxides obtained in Reference Example 1.
  • FIG. 2 illustrates a solid NMR ( 31 P MAS NMR) spectrum of phosphoric acid treated-aluminum oxide.
  • FIG. 3 illustrates FTIR spectra of aluminum oxide and phosphoric acid-treated aluminum oxide.
  • FIG. 4 illustrates results of a conversion reaction from glucose to fructose using phosphoric acid-treated aluminum oxide.
  • FIG. 5 illustrates a correlation between glucose conversion and fructose selectivity.
  • FIG. 6 illustrates results of a conversion reaction from glucose to fructose using phosphoric acid-treated aluminum oxide.
  • FIG. 7 illustrates results of a conversion reaction from glucose to fructose using phosphoric acid-treated aluminum oxide.
  • a catalyst of the present invention is a solid catalyst for a hydride isomerization reaction from glucose to fructose performed in water or in an aqueous solution, comprising a group 13 element oxide whose surface have been subjected to a phosphoric acid treatment.
  • Examples of the group 13 element oxide include aluminum oxide, gallium oxide, indium oxide and thallium oxide.
  • Examples of the aluminum oxide include ⁇ -alumina, ⁇ -alumina, ⁇ -alumina, ⁇ -alumina, ⁇ -alumina and boehmite, and ⁇ -alumina is particularly preferred.
  • Examples of the gallium oxide include ⁇ -Ga 2 O 3 , ⁇ -Ga 2 O 3 , ⁇ -Ga 2 O 3 , ⁇ -Ga 2 O 3 and ⁇ -Ga 2 O 3 , and ⁇ -Ga 2 O 3 is more preferred.
  • the indium oxide may be any In 2 O 3
  • the thallium oxide may be any Tl 2 O 3 .
  • aluminum oxide is preferred from the viewpoint of easy availability and the like.
  • the group 13 element oxide may be treated with, for example, a phosphoric acid aqueous solution of 50° C. or lower. Specifically, the group 13 element oxide may be stirred in a phosphoric acid aqueous solution of 50° C. or lower. If the phosphoric acid treatment is performed at a high temperature, phosphorylation proceeds not only in a surface portion but also to the inside of the group 13 element oxide, which is unpreferable because its function as a Lewis acid catalyst is lowered. Here, it can be confirmed through solid NMR whether the surface portion alone is phosphorylated.
  • a concentration of the phosphoric acid aqueous solution to be used may be 1 mM or more, is preferably 1 mM to 100 mM, and more preferably 10 mM to 100 mM.
  • a molar ratio between the group 13 element oxide and phosphoric acid to be used is not especially limited as long as a part of the surface of the group 13 element oxide can be phosphorylated, and 0.0001 mol or more of phosphoric acid may be used per mol of the group 13 element oxide, and 0.0001 to 1 mol of phosphoric acid is more preferably used.
  • a treatment temperature is preferably 50° C. or lower, more preferably 0 to 50° C., and is economically and further preferably 10 to 40° C.
  • a treatment time for stirring may be 5 minutes or more, preferably about 5 minutes to 48 hours, and more preferably 15 minutes to 24 hours.
  • the group 13 element oxide having the phosphoric acid-treated surface is separated from the mixture through filtration or the like.
  • the phosphoric acid is immobilized on the surface of the group 13 element oxide. This immobilization is probably caused through bond of the phosphoric acid to the surface of the group 13 element oxide, and the phosphoric acid is probably bonded in the form of —OP( ⁇ O)(OH) 2 . This bond can be checked through the solid NMR. Besides, the phosphoric acid treatment does not proceed to the inside of the group 13 element oxide.
  • phosphoric acid there is no need to subject the whole surface of the group 13 element oxide to the phosphoric acid treatment, but 0.00001 mol % or more of phosphoric acid may be immobilized on the group 13 element oxide, and preferably 0.0001 to 0.003 mol % is immobilized, and more preferably 0.0003 to 0.0015 mol % of phosphoric acid is immobilized.
  • the surface is phosphorylated and that a sufficient Lewis acid amount is kept in a surface portion. If a sufficient Lewis acid amount is kept in the surface portion and the surface is phosphorylated, a reaction from glucose to fructose selectively proceeds, and a side reaction can be inhibited.
  • the Lewis acid amount in the surface portion of the present solid catalyst is, in a state where the surface is hydrated, kept at preferably 80% or more and more preferably 85% or more of a Lewis acid amount in a dehydrated surface portion of the group 13 element oxide not subjected to the phosphoric acid treatment.
  • the Lewis acid amount is kept at more preferably 80 to 95% and further preferably 85 to 95%.
  • a Lewis acid amount can be measured based on an FTIR spectrum of a sample to which pyridine has been adsorbed.
  • the Lewis acid amount is increased as compared with that in the dehydrated surface portion.
  • This catalyst seems to excellently catalyze the hydride isomerization reaction in water or in an aqueous solution owing to this function.
  • a particle size of the group 13 element oxide having the phosphorylated surface is not especially limited, and is substantially the same as that of a particle of the group 13 element oxide used as a raw material, and for example, is preferably 0.1 to 100 ⁇ m, more preferably 1 to 100 ⁇ m, and further preferably 1 to 10 ⁇ m.
  • the group 13 element oxide having the phosphorylated surface is a solid, and after used as a catalyst, can be easily separated and collected from a reaction mixture by filtration or the like to be reused, and hence is useful as a solid catalyst.
  • the group 13 element oxide having the phosphorylated surface is useful as a solid catalyst for the hydride isomerization reaction from glucose to fructose performed in water or in an aqueous solution.
  • functionality in water or in an aqueous solution refers to a function to catalyze a reaction occurring in water or in an aqueous solution, and involves a reaction performed in an aqueous phase even if the reaction is caused in a mixed liquid of water and an organic solvent.
  • the number of solid Lewis acid catalysts thus working in water or in an aqueous solution is small.
  • the catalyst of the present invention works as a Lewis acid catalyst for the hydride isomerization reaction from glucose to fructose.
  • the catalyst of the present invention is allowed to work on glucose in water or in an aqueous solution, a side reaction is inhibited, the hydride isomerization reaction selectively proceeds, and fructose can be selectively produced.
  • a glucose concentration in the aqueous solution is not especially limited, and is preferably 0.1 to 50° by mass and more preferably 0.1 to 20% by mass.
  • An amount of the present catalyst to be used is preferably 0.01 to 10 g, and more preferably 0.1 to 1 g per gram of the glucose.
  • a reaction temperature is preferably 50 to 180° C., and more preferably 100 to 130° C.
  • a reaction time is preferably 15 minutes to 24 hours, and more preferably 30 minutes to 10 hours.
  • fructose is selectively produced from glucose, a production rate of HMF is small, and in addition, the other complicated side reactions are inhibited.
  • Selectivity in the production of fructose is remarkably excellent as compared with a case where the Sn-containing ⁇ -zeolite described in Non Patent Literature 1 or aluminum phosphate described in Non Patent Literature 2 is used.
  • Al-200 to Al-1100 refer to aluminum oxides respectively obtained at calcination temperatures of 200 to 1,100° C.
  • Ga(O-i-Pro) 3 gallium isopropoxide
  • In(O-i-Pro) 3 indium isopropoxide
  • 75 to 100 mL of 2-propanol 0.02 to 0.1 mL of acetic acid and 0.1 to 1.0 mL of water were added, and the resultant was stirred at 80° C. for 5 hours, filtrated and then dried.
  • the thus obtained precursor was calcined at 200 to 1,000° C. for 3 hours to obtain Ga 2 O 3 or In 2 O 3 .
  • BET specific surface areas of the thus obtained products are shown in Table 2. In Table 2, a numerical value following Ga 2 O 3 or In 2 O 3 indicates the calcination temperature.
  • Lewis acid amounts calculated based on FIG. 3 are shown in Table 3.
  • the Lewis acid amount in the phosphoric acid-treated aluminum oxide (hydrated) was kept at 88% of the acid amount in the dehydrated aluminum oxide. Besides, the Lewis acid amount of the phosphoric acid-treated aluminum oxide (hydrated) was larger than that of the phosphoric acid-treated aluminum oxide (dehydrated). In this manner, the Lewis acid amount of the hydrated phosphoric acid-treated aluminum oxide was sufficiently large, and hence, it was found that this phosphoric acid-treated aluminum is useful as a Lewis acid catalyst used in water or in an aqueous solution.
  • reaction vessel was charged with 0.02 g of glucose, 2 g of water and 0.05 g of phosphoric acid-treated aluminum oxide, and the resultant was stirred at 120° C. for 2 hours.
  • the thus obtained reaction solution was analyzed through high performance liquid chromatography.
  • FIG. 4 It is noted that a result obtained in using, as a catalyst, aluminum oxide not subjected to the phosphoric acid treatment is also illustrated in FIG. 4 .
  • Al represents aluminum oxide, and a numerical value following Al indicates a calcination temperature.
  • 0.1 MPP indicates the 0.1 M phosphoric acid treatment.
  • FIG. 4 It is understood from FIG. 4 that a complicated side product (unknown) was remarkably reduced and fructose selectivity was remarkably improved in using the phosphoric acid-treated aluminum oxide as compared with those obtained in using the aluminum oxide not subjected to the phosphoric acid treatment. Besides, a correlation between glucose conversion and fructose selectivity is illustrated in FIG. 5 . It is understood from FIG. 5 that the selectivity from glucose to fructose is remarkably improved by using the catalyst of the present invention.
  • the reaction was performed in the same manner as in Example 4 except that the reaction temperature for glucose was changed from 120° C. to 100° C. The result is illustrated in FIG. 7 .
  • selectivity and symbols are defined in the same manner as in FIG. 6 . It is noted that a sample with * was obtained with the reaction time for glucose set to 6 hours.

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PCT/JP2015/057015 WO2015137339A1 (ja) 2014-03-11 2015-03-10 水媒体中ヒドリド異性化反応用固体触媒

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Citations (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5139759A (en) * 1991-12-19 1992-08-18 Uop Synthesis of zeolite beta
CN1087894A (zh) 1992-11-14 1994-06-15 底古萨股份公司 生产丙烯醛的方法
WO1997047380A1 (en) 1996-06-12 1997-12-18 Project Earth Industries, Inc. Acid contacted enhanced adsorbent and/or catalyst and binder system
US5985790A (en) * 1994-12-07 1999-11-16 Project Earth Industries, Inc. Method of making acid contacted enhanced aluminum oxide adsorbent particle
WO1999058238A1 (en) 1998-05-14 1999-11-18 Coastal Catalyst Technology, Inc. The use of phosphorus to enhance the acid sites of fcc catalysts
US20060024226A1 (en) * 2002-09-16 2006-02-02 Yong-Ki Park Catalyst and method for decomposition of perfluoro-compound in waste gas
JP2007196174A (ja) 2006-01-28 2007-08-09 Osaka Industrial Promotion Organization 不均一系リン酸ジルコニウム触媒、脱水反応方法、５−ヒドロキシメチルフルフラール製造方法、セルロース分解方法、及び不均一系リン酸ジルコニウム触媒の再生方法
CN101119956A (zh) 2005-02-15 2008-02-06 阿肯马法国公司 使甘油脱水为丙烯醛的方法
US20080216391A1 (en) 2007-03-08 2008-09-11 Cortright Randy D Synthesis of liquid fuels and chemicals from oxygenated hydrocarbons
WO2011036862A1 (en) 2009-09-25 2011-03-31 Nippon Ketjen Co., Ltd. Process for producing a hydroprocessing catalyst, and method for hydroprocessing a hydrocarbon oil using said catalyst
US20110207923A1 (en) * 2010-01-15 2011-08-25 California Institute Of Technology Isomerization of sugars
WO2012108472A1 (ja) 2011-02-08 2012-08-16 財団法人神奈川科学技術アカデミー アモルファス含水チタン酸化物及びそれを含む固体ルイス酸触媒
JP2013006142A (ja) 2011-06-23 2013-01-10 Toshiba Corp 植物系材料の加水分解用触媒及び糖類の製造方法
WO2013030132A1 (fr) 2011-08-26 2013-03-07 Centre National De La Recherche Scientifique (C.N.R.S) Procede d'isomerisation du glucose en fructose
JP2013517288A (ja) 2010-01-15 2013-05-16 カリフォルニア インスティチュート オブ テクノロジー 糖の異性化
US20130150595A1 (en) * 2011-12-07 2013-06-13 James A. Dumesic Lewis and bronsted-lowry acid-catalyzed production of 5-hydroxymethylfurfural (hmf) from glucose

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7916700B2 (en) * 2004-06-30 2011-03-29 Nokia Corporation Dynamic service information for the access network
EP1959022B1 (en) * 2005-11-30 2011-08-24 Shinshu University Detection of uterine leiomyosarcoma using lmp2

Patent Citations (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5139759A (en) * 1991-12-19 1992-08-18 Uop Synthesis of zeolite beta
CN1087894A (zh) 1992-11-14 1994-06-15 底古萨股份公司 生产丙烯醛的方法
US5985790A (en) * 1994-12-07 1999-11-16 Project Earth Industries, Inc. Method of making acid contacted enhanced aluminum oxide adsorbent particle
WO1997047380A1 (en) 1996-06-12 1997-12-18 Project Earth Industries, Inc. Acid contacted enhanced adsorbent and/or catalyst and binder system
WO1999058238A1 (en) 1998-05-14 1999-11-18 Coastal Catalyst Technology, Inc. The use of phosphorus to enhance the acid sites of fcc catalysts
US20060024226A1 (en) * 2002-09-16 2006-02-02 Yong-Ki Park Catalyst and method for decomposition of perfluoro-compound in waste gas
CN101119956A (zh) 2005-02-15 2008-02-06 阿肯马法国公司 使甘油脱水为丙烯醛的方法
JP2007196174A (ja) 2006-01-28 2007-08-09 Osaka Industrial Promotion Organization 不均一系リン酸ジルコニウム触媒、脱水反応方法、５−ヒドロキシメチルフルフラール製造方法、セルロース分解方法、及び不均一系リン酸ジルコニウム触媒の再生方法
US20080216391A1 (en) 2007-03-08 2008-09-11 Cortright Randy D Synthesis of liquid fuels and chemicals from oxygenated hydrocarbons
WO2011036862A1 (en) 2009-09-25 2011-03-31 Nippon Ketjen Co., Ltd. Process for producing a hydroprocessing catalyst, and method for hydroprocessing a hydrocarbon oil using said catalyst
US20110207923A1 (en) * 2010-01-15 2011-08-25 California Institute Of Technology Isomerization of sugars
JP2013517288A (ja) 2010-01-15 2013-05-16 カリフォルニア インスティチュート オブ テクノロジー 糖の異性化
WO2012108472A1 (ja) 2011-02-08 2012-08-16 財団法人神奈川科学技術アカデミー アモルファス含水チタン酸化物及びそれを含む固体ルイス酸触媒
JP2013006142A (ja) 2011-06-23 2013-01-10 Toshiba Corp 植物系材料の加水分解用触媒及び糖類の製造方法
WO2013030132A1 (fr) 2011-08-26 2013-03-07 Centre National De La Recherche Scientifique (C.N.R.S) Procede d'isomerisation du glucose en fructose
US20130150595A1 (en) * 2011-12-07 2013-06-13 James A. Dumesic Lewis and bronsted-lowry acid-catalyzed production of 5-hydroxymethylfurfural (hmf) from glucose

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
Combined Office Action and Search Report dated Dec. 28, 2017 in Chinese Patent Application No. 201580012750.3 (with English translation of categories of cited documents), 6 pages.
Extended European Search Report dated Oct. 13, 2017 in Patent Application No. 15762249.9.
International Search Report dated Jun. 16, 2015 in PCT/JP2015/057015 filed Mar. 10, 2015.
Manuel Moliner, et al., "Tin-containing zeolites are highly active catalysts for the isomerization of glucose in water", PNAS, vol. 107, No. 14, Apr. 6, 2010, pp. 6164-6168.
V.V. Ordomsky, et al., "Glucose dehydration to 5-hydroxymethylfurfural over phosphate catalysts", Journal of Catalysis, vol. 300, 2013, pp. 37-46.

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